Many people set ambitious goals at the start of a new year, but maintaining momentum is the real challenge. One effective strategy is regular review, treating goals as directional rather than fixed. This year, the author experimented with using AI – specifically ChatGPT – to critically assess their 2026 objectives. The goal wasn’t to let the AI dictate, but to identify blind spots and prioritize realistically.
The AI as Devil’s Advocate
The core idea is to feed your goals into an AI chatbot and ask it to play devil’s advocate. The author prompted ChatGPT to analyze their list, explicitly requesting a pragmatic, unsentimental evaluation. The AI quickly identified several assumptions: unrealistic expectations about pregnancy timelines, consistent work capacity, and conflicting social commitments.
This is important because many people underestimate the physiological and emotional volatility of a year, especially when major life events like pregnancy are involved. AI can highlight these potential disruptions in a way that self-assessment often misses.
Prioritization and Trade-Offs
ChatGPT’s feedback focused on the need to prioritize ruthlessly. It asked pointed questions: Which goal would the author be willing to soften if pregnancy occurred early in the year? What does “financially stable” truly mean, emotionally? How many hours can realistically be worked without burnout?
These questions forced a clear-eyed assessment of trade-offs. The AI repeatedly emphasized that overextension – “death by a thousand quiet overextensions” – was the biggest risk. Instead of striving for growth in every area, the focus shifted to stability, especially given the possibility of maternity leave.
The Value of Constraints
The author initially resisted some of the AI’s suggestions, but ultimately acknowledged the validity of its points. ChatGPT correctly identified that cash flow would be tighter with a pregnancy, that the author had too many “soft yeses” (minor commitments adding up to overwhelm), and that a planned trip to Australia might be more disruptive than anticipated.
The final outcome was a refined list of nonnegotiables: debt payoff, front-loaded work for maternity leave, completion of key projects, and a focus on maintenance over aggressive growth. The AI’s operating rules were simple: prioritize cash reserves, work strategically with clients, and accept that stability is the success metric for the year.
AI as a Tool, Not a Replacement
This experiment demonstrates the value of AI as a critical thinking partner, not a decision-maker. ChatGPT didn’t reveal revolutionary insights, but it did force a pragmatic reassessment of priorities. The author concluded that focusing on a smaller set of nonnegotiables – just seven in this case – was more realistic than chasing a long list of wants.
The key takeaway is that AI can be a powerful tool for stress-testing goals, identifying blind spots, and clarifying what truly matters. In a year where stability is paramount, this kind of ruthless prioritization is essential.
